You know, I have a DSS wing on my singles setup. I bought it, used, six years ago. It had probably three hundred or more dives on it then. I've put probably another 500 or so on it since (maybe more). I've dived from boats and from shore, out of a car trunk or a truck bed. I'm not terribly careful with the setup, but I always put it down flat, plate underneath, and I watch carefully when I put a tank into the holders on a boat, because it's so easy to pinch the bottom part of the wing between the plate and the bench. I had a pinch flat the first year, and got a replacement bladder from Tobin. I've had no problems since.
Holes in wings happen. If you've gotten two in such a short time, I'd offer that something in the way you are transporting your gear or setting it up is putting the bladder at risk. I don't think Tobin needs to redesign his wings, as such injuries are not that common. We have, I think, at least five DSS wings, and my pinch flat is the only one we have had.